Recent regulation initiatives and the ongoing digital transition in the water sector are opening a new era in drinking water infrastructure management boosted by unprecedented funding opportunities from the post-pandemic recovery plans worldwide. These investments are not solely directed at updating equipment or replacing aging pipes, but they are geared towards enhancing the efficiency of such infrastructures. Asset management, with respect to the need of leakage reduction and control in drinking water infrastructure, is a major concern for the utilities since water loss undermines the socio-economic and environmental sustainability also with respect to energy resources. In fact, the level of water loss represents an indicator of the infrastructure’s “health” status, thus assuming importance for asset management. The effectiveness of a water loss performance indicator is a relevant issue because it guides the investment, thereby the quality of the public expenditure. The present effort aims at the detailed and scientific analysis of the effectiveness of the linear and percentage water loss indicator. The linear water loss indicator proves to be effective, because scalable, and it is the basis of novel indicator, named Asset Management Support Indicator, which can drive the quality of the expenditure for water loss reduction.